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See the Supporting Information for the preparation. No efforts were made to prepare single diastereomers since the product distribution from diastereomeric β-hydroxy sulfoxides was to be investigated.
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78651506230
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The structure could not be assigned to cyclopropanes 46 and 47 at this stage. It could be assigned only based on the NOE analysis of the acetonide derived from 59
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The structure could not be assigned to cyclopropanes 46 and 47 at this stage. It could be assigned only based on the NOE analysis of the acetonide derived from 59.
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45
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0041288450
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The inversion of sulfur configuration is expected based on precedented electrophile promoted nucleophilic sulfinyl group heterofunctionalization of alkenes, see ref 3.
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The trans -cyclopropanes corresponding to 46 and 47 are expected to react without any incident to furnish anti -anti -syn and syn -anti -syn stereotetrads. Unlike cis -allylic alcohols 42 and 43 that could be separated, the corresponding trans -allylic alcohols, obtained by reduction of 41 with Red-Al, could not be separated. Therefore further sulfoxide preparation and cyclopropanation was not attempted
-
The trans -cyclopropanes corresponding to 46 and 47 are expected to react without any incident to furnish anti -anti -syn and syn -anti -syn stereotetrads. Unlike cis -allylic alcohols 42 and 43 that could be separated, the corresponding trans -allylic alcohols, obtained by reduction of 41 with Red-Al, could not be separated. Therefore further sulfoxide preparation and cyclopropanation was not attempted.
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